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The solid-phase Nenitzescu indole synthesis

被引：61
作者：
Ketcha, DM [1 ]
Wilson, LJ
Portlock, DE
机构：
[1] Wright State Univ, Dept Chem, Dayton, OH 45435 USA
[2] Procter & Gamble Co, Pharmaceut, Hlth Care Res Ctr, Mason, OH 45040 USA
来源：
TETRAHEDRON LETTERS | 2000年 / 41卷 / 33期
关键词：
D O I：
10.1016/S0040-4039(00)00697-3
中图分类号：
O62 [有机化学];
学科分类号：
070303 ; 081704 ;
摘要：
The solid-phase version of the Nenitzescu indole synthesis of 5-hydroxyindole-3-carboxamides is reported. This process involves initial acetoacetylation of ArgoPore(R)-Rink-NH2 resin with diketene to afford a polymer-bound acetoacetamide. Formation of the corresponding enaminones via condensation with primary amines in the presence of trimethylorthoformate followed by addition of 1,4-benzoquinones leads to the desired indoles after TFA induced cleavage from the resin. (C) 2000 Elsevier Science Ltd. All rights reserved.
引用
收藏
页码：6253 / 6257
页数：5
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